Southwest® flights from Kansas City to Chicago (Midway) from $55
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Low fares from Kansas City to Chicago (Midway)
$
Kansas City (MCI)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Basic
From
$55
Seen: 1 hour ago
Kansas City (MCI)to
Chicago (Midway) (MDW)
Depart: 01/10/2026
One-way
Basic
From
$55
Seen: 1 hour ago
Kansas City (MCI)to
Chicago (Midway) (MDW)
Depart: 03/03/2026
One-way
Basic
From
$55
Seen: 1 hour ago
Kansas City (MCI)to
Chicago (Midway) (MDW)
Depart: 02/18/2026
One-way
Basic
From
$55
Seen: 2 hrs ago
Kansas City (MCI)to
Chicago (Midway) (MDW)
Depart: 03/04/2026
One-way
Basic
From
$55
Seen: 1 hour ago
Kansas City (MCI)to
Chicago (Midway) (MDW)
Depart: 01/07/2026
One-way
Basic
From
$55
Seen: 2 hrs ago
Explore flights from Kansas City to Chicago (Midway)
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
Flight Details
Departing from:
Kansas City International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
1 hour 23 minutes
Distance:
405 miles
Route Information
156† Weekly flights
- 6‡ Nonstop flights per day Monday through Friday
- 5‡ Nonstop flights on Saturday
- 7‡ Nonstop flights on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore Chicago (Midway)
When you think of the City of the Big Shoulders, there’s a good chance you picture the iconic skyline. When you visit Chicago, you can take in the view by land or sea (or, more accurately, lake or river) with popular tours, or you can view the skyline from within it. The Chicago Skydeck Ledge lets you step four feet out from the building, placing you 1,353 feet above the busy streets of downtown Chicago. If your nerves don’t take your breath away, the view sure will.
There’s more to see in Chicago than the skyline, of course. Museum fans are in for a treat and should consider a trip to one of the several that the city boasts. The Art Institute, the Field Museum, the Museum of Contemporary Art, the American Writers Museum, and the Museum of Science and Industry are all conveniently located near the Loop (what locals call the city’s downtown); the Chicago History Museum is further north, but should not be missed for true lovers of the town. More interested in flora and fauna than man-made masterpieces? Chicago boasts the Shedd Aquarium and Lincoln Park Zoo inside city limits, Brookfield Zoo in the western suburbs, and the Chicago Botanic Gardens in the northern suburbs. The latter two are easily accessible via Metra train.
Questions we hear the most
The average flight time from Kansas City to Chicago (Midway) is 1 hour 23 minutes.
There are 156 weekly flights from Kansas City to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Kansas City to Chicago (Midway) 6 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Kansas City to Chicago (Midway) 5 times per day on Saturdays and 7 times per day on Sundays.
To find the lowest fares by day and time to fly Kansas City to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from Kansas City to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Kansas City
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.